ie. extra cash out means no hole!

He will hopefully have extra equity built in to the deal but the difference between a $30k and $40k house market wise may not be anything.

I would believe most people are not able to put extra cash towards a remodel after buying a house. 

You can deploy that extra capital now while interest rates are low.

If I had to pay an extra 1-2k to have it taken care of by a PM (which I will hire anyway since I don't want to manage the property myself - I'll be a first time landlord) I would rather go that route.Any advice / tips / feedback would be greatly appreciated.

But, it comes down to your risk aversion: many people in your position (1-8 rentals) have their rentals attached to their Homeowners insurance and then have a personal umbrella for extra protection.  

If push comes to shove I could 'create' some money for an extra month or two.

So when you are driving through town, make an extra stop by these places that could benefit by leasing from you.

Either way it looks like I will be doing month to month then and spending the extra money to give the resort atmosphere to include wifi, laundry facility, etc.I use my own lease that I drew up and fined tuned over several years after evaluating many other leases and through personal experiences.  

Lumberjack cleaning, we have a few local commercial cleaning clients that I still operate out of Portland for extra income.